Fungicidal substituted furancarboxylic acid cycloalkylamide

ABSTRACT

2,5-DIMETHYL-5-FURAN-3-CARBOXYLIC ACID CYCLOHEXYLAMIDE WHICH HAS A GOOD FUNGICIDAL ACTION AND A PROCESS FOR CONTROLLING FUNGI WITH THIS COMPOUND.

United States Patent 1 1 1111 3,903,293

Distler et al. Sept. 2, 1975 [5 FUNGICIDAL SUBSTITUTED [58] Field of Search 424/285; 260/3473 FURANCARBOXYLIC ACID CYCDOALKYLAMIDE [56] References Cited [75] Inventors: Harry Distler, Ludwigshafen; Rudi UNITED STATES PATENTS Widder, Eppelheim; Ernst-Heinrich 3,352,663 11/1967 Freund et a1. n 2.5

Pommer, Limburgerhof, all of Germany Division of Ser. No. 131,545, April 5, '1971, Pat. No. 3,862,966.

Assignee:

Foreign Application Priority Data Apr. 23, 1970 Germany 2019535 US. Cl. 424/285 Int. Cl A0ln 9/28 FOREIGN PATENTS OR APPLICATIONS 2,006,471 8/1970 Germany 39-26571 H1964 Japan 1,914,954 10/ l 969 Germany 1,2 15,066 12/ 1969 United Kingdom Primary Examiner-Albert T. Meyers Assistant Examiner-Douglas W. Robinson Attorney, Agent, or FirmJohnston, Keil, Thompson & Shurtleff [5 7] ABSTRACT 2,5-dimethy1-5-furan-3-carb0xy1ic acid cyclohexylamide which has a good fungicidal action and a process for controlling fungi with this compound.

7 Claims, N0 Drawings FUNGICIDAL SUBSTITUTED FURANCARBOXYLIC ACID CYCLOALKYLAMIDE This is a division of application Ser. No. 131,545, filed Apr. 5, I971, now US. Pat. No. 3,862,966.

e.g., the keto group, the ether group, the ester group or the amide group, this group or these groups being attached as substitucnt( s) to a hydrocarbon ring or being a component of a hetcrocyclic ring, may be used as The present invention relates to a new and valuable spray liquids. substituted furancarboxylic acid cycloalkylamide and A u formulations may be pepared from emulfuhgicides cohtaihihgrthis Compouhdsion concentrates, pastes or wettable powders by add- It is known to use tetramethylthiuram disulfidc for i water, T prepare emulsions the ingredients as such controlling fuhgi- It is also known that suhsthutcd or dissolved in a solvent may be homogenized in water f r n r y acid anihdes g or organic solvents by means of wetting or dispersing l-methylfuran-3-carboxanilidc and agents, e.g., polyethylene oxide adducts. Concentrates 3-methylfuran-2-carboxanilide (German Printed Apwhich are suitable for dilution with water may be pre- Phcatioh N9 1,914,954) exhibit fungicidal activitypared from active ingredient, emulsifying or dispersing We have now found that 2,5-dimethylfuran-3- agent and possibly solvent. Compounds having adecarboxylic acid cyclohexylamide has a gOOd fungicidal l5 quate basicity may be used as salts in aqueous solution action. This action is particularly in evidence on fungi even after formation of the salt. of the Basidiomycetes class such as rust fungi in crop Dusts may b prepared b i i or i di the Plants, and 0h soll'borhe fuhgh Such as Rhlzoctoma tive ingredients with a solid carrier, e.g., kieselguhr, solani and Sclerotium rolfsii. The compound is also eftalc, clay or f tili fective Plant Pathogens f may be trahsmittfzd The good fungicidal action of the compound of this seeds such Fusanum Wale (Show mcld) and invention is demonstrated in the following examples. niperdous fungi, such as Coniophora cerebella.

The preparation of the compound of the invention is illustrated in the following example. EXAMPLE 2 EX M 1 The active ingredients are dissolved in acetone in At a to 1535 parts by weight of amounts of 0.01 and 0.005% (by we1ght) and umformly dimethyl-3-furancarboxylic acid chloride and 10.1 dlspersefl m q nufrlem again h agar 18 parts of triethylamine are added to 9.9 parts of cyclopoured lhto dlshes havmg a (hameter of 9 hexylamine in 50 parts of ethylene chloride. After stir- After the g has solidified, the dishes are Centrally ring for 3 hours at C, parts of water is added and oculated with mycelium flakes of Rhizoctonia solani, the organic phase separated. After drying the orga i Sclerotium rolfsii, and Coniophora cerebella, and cophase with Na SO,,, the solvent is removed at subatmonidia of Fusarium nivale. The dishes are incubated at spheric pressure. 25C and the extent of the development of the fungus Yield: 21.4 parts (96.8% of theory) of 2,5 35 colony i a e ed after 6 days. dimethylfuran-3-carboxylic acid cyclohexylamide as colorless crystals. 0 no fungus growth Melting point: 1 18 to l 19C (recrystallized from pe- 1 di f fungus Colony 05 to 1,5 cm troleum ether) l3 19 2 (molecular Weight: 40 2 diameter of fungus colony 1.5 to 3.5 cm Gulch; C H O N 3 diameter of fungus colony 3.5 to 4.5 cm

70.5% 8.6% 14.5% 6.4% 4 diameter of fungus colony 4.5 to 7 cm fmmd: 5 diameter of fungus colony 7 to 9 cm Active Rhizoctonia Sclerotium rolfsii Coniophora Fusarium ingredient snlani '71 age of active ccrcbella nivalc age of active ingredient in agar "/1 of active 7: age of ingredient in ingredient active in agar in agar grcdicnt in 0.01 0.005 (1.01 0,005 0.01 0.005 agar Example 1 0 0 o o 0 o 0 o Tetramethylthiuram di- 4 4 3 4 4 5 2 3 sulfide (comparativc agent) Control 5 5 5 5 (untreated) The fungicides according to this invention may be EXAMPLE 3 used as solutions, emulsions, suspensions or dusts. The

than 150C and one or more than one functional group,

Leaves of pot-grown bean plants of the Saxa variety are artificially infected with spores of bean rust (Uromyces appendiculatus) and placed in a steam-saturated chamber for 24 hours at 22 to 24C. The plants are then sprayed with aqueous emulsions consisting of 80% of active ingredient and 20% of emulsifier and left in a greenhouse at 22 to 25C and a relative humidity of 60 to Fungus attack is assessed after 8 days.

Active Extent of attack after treatment with spray containing ingredient ().l, 0.05 and 0.025% of active ingredient Example I 0 0 Control (untreated) 0 no fungus attack. graduated down to 5 leaves completely covered EXAMPLE 4 70 parts by weight of the compound of Example 1 is mixed with 30 parts by weight of N-methyl-apyrrolidone. A mixture is obtained which is suitable for application in the form of very fine drops.

EXAMPLE 5 20 parts by weight of the compound of Example 1 is dissolved in a mixture consisting of 80 parts by weight of xylene, parts by weight of the adduct of 8 to 10 moles of ethylene oxide to 1 mole of oleic acid-N- monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.

EXAMPLE 6 20 parts by weight of the compound of Example 1 is dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide to 1 mole of isooctylphenol, and 10 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring the solution into l00,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.

EXAMPLE 7 20 parts by weight of the compound of Example 1 is dissolved in a mixture consisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210 and 280C, and 10 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil. By

pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.

EXAMPLE 8 20 parts by weight of the compound of Example I is well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthaleneoz-sulfonic acid, 17 parts by weight of the sodium salt of a ligninsulfonic acid obtained from a sulfite waste liquor, and 60 parts by weight of powdered silica gel, and triturated in a hammer mill. By uniformly distributing the mixture in 20,000 parts by weight of water, a spray liquid is obtained containing 0.1% by weight of the active ingredient.

EXAMPLE 9 3 parts by weight of the compound of Example 1 is intimately mixed with 97 parts by weight of particulate kaolin. A dust is obtained containing 3% by weight of the active ingredient.

EXAMPLE 10 30 parts by weight of the compound of Example 1 is intimately mixed with a mixture consisting of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel. A formulation of the active ingredient is obtained having good adherence.

We claim:

1. A process for controlling growth of fungi which comprises contacting fungi of the Basidiomycetes class with a fungicidal amount of 2,5-dimethylfuran-3- carboxylic acid cyclohexylamide.

2. A process as claimed in claim 1 wherein said fungi are on crop plants, and the fungicidal amount of 2,5- dimethylfuran-3-carboxylic acid cyclohexylamide is applied to leaves of said plants.

3. A process as claimed. in claim 1 wherein said fungi are soil-borne fungi.

4. A process as claimed in claim 3 wherein said fungi are Rhizoctania solani or Sclerotium rolfsii.

5. A process as claimed in claim 1 wherein said fungi are plant pathogens transmitted via seeds.

6. A process as claimed in claim 5 wherein said fungi 'are Coniphoro cerebella.

7. A process for controlling growth of Fusarium nivale fungi which comprises contacting said fungi with a fungicidal amount of 2,S-dimethylfuran-3-carboxylic acid cyclohexylamide. 

1. A PROCESS FOR CONTROLLING GROWTH OF FUNGI WHICH COMPRISES CONTACTING FUNGI OF THE BASIDIOMYCETES CLASS WITH A FUNGICIDAL AMOUNT OF 2,5-DIMETHYLFURAN-3-CARBOXYLIC ACID CYCLOHEXYLAMIDE.
 2. A process as claimed in claim 1 wherein said fungi are on crop plants, and the fungicidal amount of 2,5-dimethylfuran-3-carboxylic acid cyclohexylamide is applied to leaves of said plants.
 3. A process as claimed in claim 1 wherein said fungi are soil-borne fungi.
 4. A process as claimed in claim 3 wherein said fungi are Rhizoctania solani or Sclerotium rolfsii.
 5. A process as claimed in claim 1 wherein said fungi are plant pathogens transmitted via seeds.
 6. A process as claimed in claim 5 wherein said fungi are Coniphoro cerebella.
 7. A process for controlling growth of Fusarium nivale fungi which comprises contacting said fungi with a fungicidal amount of 2,5-dimethylfuran-3-carboxylic acid cyclohexylamide. 